Hydrochloric Acid → 4-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

HRID 249051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249051
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([N:7]([CH2:19][CH3:20])[CH2:8][CH2:9][O:10]C(=O)C2C=CC=CC=2)=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.C(OCC)C>CO.O>[CH2:19]([N:7]([CH2:8][CH2:9][OH:10])[C:6]1[CH:21]=[CH:22][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)[CH3:20]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 1045642-(N-Ethyl-4-formylanilino)ethyl benzoate

Produkt 1

HCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehydeAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Formyl-N-ethyl-N-(2-benzoyloxyethyl)aniline (16 g, 51 mmol) was added to a stirring suspension of potassium carbonate (9 g, 65 mmol) in methanol (150 mL) and water (50 mL). Stirring was continued at room temperature for 4 hours followed by addition of 1 molar hydrochloric acid (250 mL) and extraction into diethyl ether (3×100 mL). The combined ether layers were washed with saturated sodium bicarbonate (200 mL), water (200 mL), saturated sodium chloride (200 mL), dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified using a silica gel chromatography column eluting with 50% ethyl acetate in hexane which gave the compound as a clear yellow oil (5 g, 51% yield).

Aufarbeitung

  1. washThe combined ether layers were washed with saturated sodium bicarbonate (200 mL), water (200 mL), saturated sodium chloride (200 mL)
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified
  5. washeluting with 50% ethyl acetate in hexane which

Quellen und Nachweise

ORD-Eintrag
ord-7d992ac09afe4dee9848fa024a9ee2ae
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212269

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